HCID 15171823, compound → HCID 15171898, compound

HRID 654511Notes

Reaction equation

HRID 654511 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:13]#[C:14][C:15]2([CH3:29])[CH2:20][CH2:19][C:18]3[C:21]([CH3:28])=[C:22]([OH:27])[C:23]([CH3:26])=[C:24]([CH3:25])[C:17]=3[O:16]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][C:15]2([CH3:29])[CH2:20][CH2:19][C:18]3[C:21]([CH3:28])=[C:22]([OH:27])[C:23]([CH3:26])=[C:24]([CH3:25])[C:17]=3[O:16]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15171823HCID 15171823, compound

Product 1

HCID 15171898HCID 15171898, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.7 g of rac-2-{2-[3-(acetyloxy)-4-methoxyphenyl]ethynyl}-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol, 0.2 g of 5% palladium on carbon and 50 ml of ethanol was hydrogenated at atmospheric pressure for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. Crystallization from ether/hexane gave 0.6 g of colorless crystals with m.p. 110°-113°.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customCrystallization from ether/hexane

Sources & evidence

ORD record
ord-ea9a5be5f5f5466cb191f69a74f4b85e
Source dataset
uspto-grants-1992_07
Patent number
US05132310

Reaction notes

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